Transformations of Morphine Alkaloids by Pseudomonas putida M10Marianne T. Long, Anne M. Hailes, Gordon W. Kirby, and Neil C. BruceApplied and Environmental Microbiology, 61(10), 3645–3649 (1995)
The oxidation of morphine by washed-cell incubations of Pseudomonas putida
M10 gave rise to a large number of transformation products including hydromorphone (dihydromorphinone), 14?-hydroxymorphine, 14?-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14?-hydroxydihydromorphinone) as substrate, the major transformation product was identified as oxymorphol (14?-hydroxydihydromorphine). The identities of all these biological products were confirmed by mass spectrometry and 1
H nuclear magnetic resonance spectroscopy. This is the first report describing structural evidence for the biological synthesis of 14?-hydroxymorphine and 14?-hydroxymorphinone. These products have applications as intermediates in the synthesis of semisynthetic opiate drugs.